Diethyl Ether → 2-Chloro-β-hydroxy-5-methyl-α-methylene-3-pyridinepropanenitrile

HRID 1445544Notes

Reaction equation

HRID 1445544 reaction equation
[Cl:1][C:2]1(C=O)[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][NH:3]1.C1[N:16]2[CH2:17][CH2:18]N(CC2)C1.[C:19](#N)C=C.[CH2:23]([O:25]CC)C>>[Cl:1][C:2]1[C:7]([CH:23]([OH:25])[C:18](=[CH2:19])[C:17]#[N:16])=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 7855AcrylonitrileHCID 9237DabcoHCID 86612627HCID 86612627, compound

Product 1

HCID 444053562-Chloro-β-hydroxy-5-methyl-α-methylene-3-pyridinepropanenitrile

Procedure

To a mixture of 2-Chloro-5-methylpyridinecarboxaldehyde (10 mmol, 1.55 g) and DABCO (10 mmol. 1.12 g) was added an acrylonitrile (60 mmol.) under neat conditions [solvent free conditions] at room temperature and the reaction progress was monitored by TLC. Upon completion of the reaction mixture (˜4-5 min.) was diluted with diethyl ether (300 mL) and washed with water 3×50 mL. The organic layer was dried over Na2SO4 and concentrated, the residue was subjected to column chromatography over silica gel, eluting with ethyl acetate and hexane (2:8, v/v) to give the desired product in almost quantitative (2.05 g).

Workup

  1. washwashed with water 3×50 mL
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. washeluting with ethyl acetate and hexane (2:8, v/v)

Sources & evidence

ORD record
ord-3a06fcad6c3e464e9d2d41f955bfd8b5
Source dataset
uspto-grants-2010_02
Patent number
US07666883B2

Reaction notes

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